1,4-Dioxane → HCID 66997575, compound

Participants

Reaction Steps

In a 4 mL vial tert-butyl(S)-1-((3aR,4S,6aS)-2-(2-fluorophenyl)octahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate from Step 2 (72 mg, 0.161 mmol) was dissolved in 4 N HCl in 1,4-dioxane (1 mL, 4.00 mmol). An oil slowly gummed out of solution. The reaction was stirred at room temperature for 18 hours, and the solvent was removed under a stream of nitrogen. The crude material was purified using a 12 g silica gel cartridge with 1-10% methanol (2 N ammonia)/dichloromethane to give N-[(3aR,4S,6aS)-2-(2-fluorophenyl)octahydrocyclopenta[c]pyrrol-4-yl]-N2-methyl-L-leucinamide: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.29 (d, J=7.4, 1H), 7.16-7.09 (m, 1H), 7.06 (tt, J=4.8, 2.4, 1H), 6.86-6.78 (m, 2H), 4.49-4.41 (m, 1H), 3.67 (d, J=9.6, 1H), 3.31-3.23 (m, 2H), 3.21 (d, J=9.5, 1H), 3.11 (dd, J=9.3, 7.0, 1H), 2.71-2.63 (m, 2H), 2.45 (s, 3H), 2.14-1.95 (br m, 1H), 2.10 (td, J=12.1, 6.1, 1H), 1.99-1.87 (m, 2H), 1.74 (ddd, J=13.7, 7.8, 5.9, 1H), 1.69-1.57 (m, 2H), 1.49-1.40 (m, 1H), 0.94 (t, J=4.5, 3H), 0.87 (d, J=6.6, 3H); MS (ESI+) m/z 348 (M+H)+.

Provenance & Evidence